The Greatest Blackjack Wins of All Time

January 17, 2021

Blackjack is one of the oldest and most popular card games in the world. Being simple and attractive at the same time, it has easily conquered the hearts of gamblers from all over the globe.

Although today we have plenty of game variants to select from, the basic rules have never changed. The game is particularly popular among highrollers which is why we’ve had the chance to witness some crazy stories involving streaks worth millions of dollars over the course of history.

Anyone who walks into a casino dreams of a massive life-changing win. Sadly, one a very small portion of players see their dreams come true. Common people have a greater chance to hit a million jackpot on progressive slot machines.

Blackjack is different as you can’t quite win millions by betting a couple of bucks. This is why the list of the most successful blackjack winners mainly includes wealthy people who had already been millionaires before enlarging their bankrolls at a blackjack table. There are always some exceptions, though, and you are about to find them on this list.

As you might have guessed from the title and the introduction part, we are going to highlight the ten biggest blackjack wins of all time. We did not only count wins on a single night as streaks of several months and even years (in one case) are included. It is the best way to show the most skilled blackjack players in the history of the game. Stay tuned and enjoy the list that features some incredible stories worth reading.

10 – A Taxi Driver Switches from Roulette to Blackjack – A Move worth $132,000

As mentioned in the introduction, we all dream (in our imagination) of a jackpot win that would change our lives once and for all. There is a man who had a real dream of winning big. He told his wife about it just several days before walking into Westcliff Casino in Western Esplanade. The man was a taxi driver named Goksel Selay.

According to his words, he had never enjoyed luck with any kind of gambling. Nevertheless, it did not prevent the man to try and make his dream come true. It was a quiet evening for fares and the taxi driver decided to enter the casino.

The Kent-native began by playing roulette. As he lacked success there, he moved onto a blackjack table after noticing the significant jackpot growth. It proved out to be one of the best decisions of his life as the father-of-two was dealt for aces to win the “Blackjack Aces” jackpot worth $132,000. And then you say dreams do not come true. They well did for this 53-year-old.

9 – An amateur Gambler Scoops $470,000 at a Bellagio

Those who have watched Ocean’s 11 starring Brad Pitt and George Clooney know at least one amazing story about Bellagio. If there is someone who has missed the movie, we’d warmly advise it.

Nevertheless, Pitt and Clooney were actors in a movie about a group of people who stole the money from the vault at Bellagio. What you are about to read now is not a movie. It is a true real-life story about an amateur gambler who has claimed almost half a million dollars by playing blackjack at one of the most famous Las Vegas casinos.

His name is Michael Geismar. He is a hedge fund manager who liked to play blackjack whenever he had the chance. It is worth mentioning that these were only rare occasions. Back in 2012, Geismar attended a business convention in Las Vegas. He spent days at a convention and nights at Bellagio.

Since he had never been a super passionate gambler, it was no wonder he decided to play $100 a hand. Nevertheless, Michael suddenly decided to raise the stakes as he got incredibly hot. He laid down $10,000 a hand before he knew it. While the experts would have never recommended such an aggressive strategy, it has well paid off for Geismar who left the iconic casino $470,000 richer. Cool run for a man who plays blackjack just a few times a year, right?

8 – World Series of Blackjack Winners

World Series of Blackjack is a TV show tournament produced by GSN cable network. It is the blackjack’s version of a much popular World Series of Poker. To enter the show, the players have to earn an invitation or win a series of satellite events. The show made a debut in March 2004 and lasted for no more than four seasons (until 2007).

You must ask yourself what this show has to do with the list of the biggest blackjack winners. Well, the answer lies in the grand prize for the final table winner. It went from $100,000 in the first season to a whopping $500,000 in the fourth. The maiden winner was Mike Aponte, a member of the legendary MIT team we are going to speak about at the end of the article. He dispatched “Hollywood” Dave Stann in the final, clinching the $100,000 main reward on the occasion.

The next winner was Ken Einiger who claimed $250,000 the following year. Finally, the winners of the next two seasons enjoyed the greatest rewards. Dr. Jeff Bernstein and Alice Walker scooped $500,000 apiece in 2006 and 2007 respectively.

7 – Oscar-winning Actor Banned from Playing Blackjack at Hard Rock after a Whopping Win

We spoke about George Clooney and Brad Pitt above in the article. While they were only actors who played in a movie about a famous Las Vegas casino, their equally popular colleague Ben Affleck has been a real-life protagonist in one of the best blackjack streaks Las Vegas has ever seen.

Ben visited Vegas to spend some time with his lovely wife Jennifer Garner before flying to Detroit to shoot the new Batman movie. Besides Jen, he was in love with card games, blackjack in particular. He thus strolled into the Hard Rock Casino to practice one of his favorite activities. The Oscar-winning actor then quickly got on a super-hot streak, the one that has secured him a staggering $800,000 win.

The casino managers then approached Ben to tell him he was no longer allowed to play blackjack in their property. Interestingly, the staff was super friendly to him, even offering a romantic couple a car as compensation. Ben has never again played blackjack at the Hard Rock Casino, but an $800,000 win has certainly earned him an honorable place in our list.

6 – A Homeless Man Wins $1.5 Million in Five Days at Treasure Island

Remember that we mentioned exceptions to the general rule that only wealthy people can win big at blackjack? We’ve come to one. Right now, you are about to read one of the most incredible gambling stories in general.

The setting is Las Vegas, the protagonist truly unique, and the casino owner is one of the most famous Sin City figures. We’ll go back to early-April 1995. A barefoot man who was in his eighties at the time walked into Steve Wynn’s Treasure Island and Casino. Yes, you heard right. It was a homeless man whose wife had chucked him out earlier. He cashed in his $400 Social Security check and decided to spend it at a casino.

A terrible decision when you are in such a situation, most people would say. You can bet as low as $5 and as big as $10,000 a hand while playing blackjack at Treasure Island. His entire pension and wealth were just $400. The homeless man took advantage of free drinks, ordering Jack Daniels and Coke. However, he then got into one of the most shocking runs the casino industry has ever witnessed. Shoeless Joe (we only know his name) turned the government check into $1.5 million in no more than five days.

He sold the story to Steve Wynn for $10,000 and received a complimentary room at the hotel, security guards, and even a limousine. Rumors say the Shoeless Joe had then lost the majority of his winnings and resumed to the old life style.

5 – UFC President Banned from Palms Casino after Winning $2 million in Three Months

We’ve told Ben Affleck’s story above in the article. Well, the Oscar-winning actor is not the only celebrity blackjack champion here. The high fifth place in the list is held by Dana White. The UFC President had two disputes with the Palms Casino Resort, both times after being banned for his significant wins at blackjack tables.

Dana White claims he has never been a card counter but who can trust him? Could you believe these major winnings were merely a product of lucky streaks? We do not believe him, but certainly, respect what he has done at these blackjack tables in Sin City.

Dana White was first banned from the Palms Casino in 2012. However, the new chief executive Dan Lee sent him a personal invitation to return to the table two years later. White was flattered with a $5k worth bottle of 2001 Domaine de la Romanee-Conti Montrachet and he was happy to get back to his beloved game.

Nevertheless, it was a move the new Palms Casino CEO would soon regret as Dana White won another $2 million over three months. He would have probably gone to larger sums had his limit per hand not been cut from $25,000 to $5,000.

4 – Blackjack Hall of Famer and the Card Counting Pioneer

One can simply not talk about the history of blackjack without mentioning Ken Uston. The New York City-born man is widely known as one of the most successful blackjack players of all time. He was one of the maiden people to have entered the Blackjack Hall of Fame which is the best recognition of his strong impact on the advanced strategies of the game.

Ken was a natural talent who still spent hours and hours to bring his skills to perfection. One of the card counting pioneers has gathered a team of mathematicians and experts who have been popular even before the great MIT group. According to the reports, his team took around $4.5 million over six years from several Las Vegas casinos.

3 – A millionaire Wins $15.1 million, Courtesy of a Loss Rebate

Speaking of legends, we can by no means skip Don Johnson. One of the most famous likes in the blackjack history scooped more than $15 million over just five months and he has done so without card counting. Mr. Johnson brutally slaughtered three Atlantic City casinos in late-2011 and early-2012. He was not a card counter, but we can certainly not consider him simply a lucky highroller either.

According to his words, the blackjack version he played had only a 0.263% house advantage. Now, the common practice for Las Vegas casinos was to pay a certain percentage of a loss rebate to highrollers who spent a certain number of hours at the tables.

Don negotiated a 20% refund on losses any time he lost more than $500,000. So, all he needed to do was to quit either after winning $2.4 million or losing $2.6 million. Such a strategy has helped Don Johnson, who had already been a millionaire, claim $6 million at Tropicana, $5 million at Borgata, and $4 million at Caesars, all within a five-month period. A solid strategy we reckon.

2 – The Biggest Single Session Win Ever

The second place is reserved for the biggest individual blackjack win of all time. It is courtesy of another millionaire, Kerry Packer. They say luck is with the brave ones. It is easy to be brave when you are a millionaire, you can reckon.

However, it is very hard to explain the amount of luck Mr. Kerry Packer has had on two separate occasions. We will begin his story with a 1991 win. Packer scooped a staggering $7 million in just one night at the Hilton Casino in Las Vegas.

He returned to Sin City four years later, this time at MGM Grand Casino. Packer decided to bet $250,000 a hand, playing as many as eight hands at the same table simultaneously. The hottest gambling streak ever resulted in a whopping $40 million profit for the man in no longer than 40 minutes.

According to the reports, Mr. Packer left an incredible $1 million tip to the dealer. Speaking of luck, it has not always been on Packer’s side as Kerry reportedly lost more than $27 million in ten months after the mentioned wins. Either way, the $40 million win at MGM Grand will be remembered forever in the blackjack history books.

1 – The Most Legendary Blackjack Story Ever

The entire world came to know about an enormous success a group of the most talented MIT students has had after watching “21”. A movie featuring Kevin Spacey in the main role has become a massive blockbuster and by far the most popular gambling movie ever recorded.

The movie was based on a true story, telling the story of Bill Kaplan’s life. Bill was a Harvard graduate who turned $1,000 into $30,000 in nine months, beating the system by card counting. A group of MIT students was amazed by how Bill Kaplan made a small fortune by playing cards. He told them everything about the process and they soon formed a team of 80 of the most talented students from the most esteemed universities, including MIT, Harvard, Yale, etc.

The students divided them into several teams who played at different casinos on different nights. They simply followed the pre-arranged scheme, trusted each other, and took casinos on a big ride. Although there is no 100% accurate information on the total sum of the winnings, the group is believed to have won between $50 and $100 million. Although we’ve seen some iconic stories in the article, this is without doubts the most legendary one.